4-{2-[(2R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}(2H4)benzonitrile

• ChemBase ID: 177383
• Molecular Formular: C22H17F2N5OS
• Molecular Mass: 437.4650864
• Monoisotopic Mass: 437.11218763
• SMILES: c1c(c(cc(c1)F)F)C([C@H](c1scc(n1)c1ccc(cc1)C#N)C)(O)Cn1cncn1
• Canonical SMILES: N#Cc1ccc(cc1)c1csc(n1)[C@@H](C(c1ccc(cc1F)F)(Cn1cncn1)O)C
• InChI: InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22?/m0/s1
• InChIKey: OPAHEYNNJWPQPX-XLEXHMCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[(2R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}(^2H₄)benzonitrile
• IUPAC Traditional name: 4-{2-[(2R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}(^2H₄)benzonitrile
• Synonyms: 4-[2-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile-d4; [R-(R*,R*)]-4-[2-[2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile-d4; BMS 207147-d4; ER 30346-d4; Ravuconazole-d4

Database IDs

• PubChem SID: 164233293
• PubChem CID: 71751989

CALCULATED PROPERTIES

• Acid pKa: 12.683222
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.143128
• LogD (pH = 7.4): 4.143493
• Log P: 4.1435003
• Molar Refractivity: 123.9407 cm^3
• Polarizability: 43.195774 Å^3
• Polar Surface Area: 87.62 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 148-151°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R128002

Ergosterol biosynthesis inhibitor. Antifungal.

REFERENCES

• Fung-Tomc., J.C., et al.: Antimicrob. Agents Chemother., 42, 313 (1988)
• Tsuruoka, A., et al.: Chem. Pharm. Bull., 46, 623 (1988)
• Gupta, A.K., et al.: J. Eur. Acad. Dermatol. Venereol., 19, 437 (1988)